Will US customs have records of someone entering the US (in 1989) and exiting (in 1991)? It was before machine-readable passports

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Does anyone know anything more concrete than my guess?

By default you should presume that the US government does know and build up your strategy accordingly. Your options are therefore:

  1. Best approach: apply for a US visa, honestly mentioning your previous overstay. Assuming you're an otherwise law-abiding individual with a stable source of income its highly likely you will receive a visa regardless of your previous overstay.
  2. Risky approach: fly to Canada and then enter the US overland, without applying for an ESTA or a visa. At the land border you are usually not asked about previous overstays and the crossing experience is quite smooth. But if you are asked, the best strategy would be to tell the truth and hope for the best. In the worst case scenario you can just drive back to Canada and enjoy a holiday there instead.

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